Polyether group containing dental composition containing an F-containing compound, process of production and use thereof
View Patent ↗The invention relates to a curable dental composition comprising a curable polyether group containing polymer as component (A), an initiator capable of initiating a curing reaction of component (A) as component (B) and a certain F-containing compound as component (C). The invention also relates to a method of production and use of the curable dental composition or a respective kit of parts for the preparation of or as impression material or for the preparation of crowns and bridges.
1. A curable dental composition comprising
a curable polyether group containing polymer as component (A), component (A) being a compound comprising polyalkylene oxide moieties,
an initiator capable of initiating a curing reaction of component (A) as component (B),
an F-containing compound as component (C),
wherein the F-containing compound is selected from the group of
Rf—(O) t —CHF—(CF 2 ) x -T, with t=0 or 1, x=0 or 1 and Rf being a linear or branched per- or partly fluorinated alkyl chain, wherein the per- or partly fluorinated alkyl chain can be interrupted by O atoms, with the proviso that when t is 0, Rf is a linear or branched per- or partly fluorinated alkyl chain interrupted by at least one oxygen atom,
Rf—(OCF 2 ) m —O—CF 2 -T, with m=1 to about 6 and Rf being a linear or branched per- or partly fluorinated alkyl chain, wherein the per- or partly fluorinated alkyl chain can be interrupted by O atoms,
CF 3 —(CF 2 ) 2 —(OCF(CF 3 )—CF 2 ) z —O-L-T, with z=0, 1, 2, 3, 4, 5, 6, 7 or 8 and L having a structure selected from —CF(CF 3 )—, —CF 2 — and —CF 2 CF 2 —,
Rf—(O—CF 2 CF 2 ) n —O—CF 2 -T, with n=1, 2, 3, 4 or 5 and Rf being a linear or branched per- or partly fluorinated alkyl chain, wherein the per- or partly fluorinated alkyl chain can be interrupted by O atoms,
wherein T is selected from —COOR, —CONR b R c —CH 2 OH, —CF 2 OR, —CHFOH, —CHFOR, —CH 2 OR or —F with R being a linear or branched alkyl (C1 to C9), aryl chain (C1 to C9) or alkylaryl (C1 to C9) each of which may optionally be substituted with one or more substituents selected from the group consisting of hydroxyl, amino group, halogen atom, an SiH group and a group capable of reacting with SiH, R b and R c independently representing H or having a meaning as given for R.
2. The dental composition of claim 1 , wherein the F-containing compound is selected from
Rf—O—CHF-T, with Rf being a linear or branched per- or partly fluorinated alkyl chain (C1 to C6), which can be interrupted by oxygen atoms,
Rf—O—CHF—CF 2 -T, with Rf being a linear or branched per- or partly fluorinated alkyl chain (C1 to C6), which can be interrupted by oxygen atoms,
Rf—(O—CF 2 ) u —O—CF 2 -T, with Rf being a linear or branched per- or partly fluorinated alkyl chain (C1 to C6), which can be interrupted by oxygen atoms, and u=1, 2, 3, 4, 5 or 6,
Rf—(O—CF 2 —CF 2 ) k —O—CF 2 -T, with Rf being a linear or branched per- or partly fluorinated alkyl chain (C1 to C6), which can be interrupted by oxygen atoms, and k =1, 2, 3, 4 or 5,
CF 3 —(CF 2 ) 2 —(OCF(CF 3 )—CF 2 ) z —O—CF(CF 3 )-T, with z=0, 1, 2, 3, 4, 5, 6, 7 or 8,
and mixtures thereof,
T having the meaning as defined in claim 1 .
3. The dental composition of claim 1 , wherein the F-containing compound is selected from
CF 3 —(O—CF 2 ) 3 —O—CF 2 -T
CF 3 —(O—CF 2 ) 5 —O—CF 2 -T
C 2 F 5 —(O—CF 2 —CF 2 ) 1 —O—CF 2 -T
C 3 F 7 —(O—CF 2 —CF 2 ) 1 —O—CF 2 -T
C 4 F 9 —(O—CF 2 —CF 2 ) 1 —O—CF 2 -T
C 2 F 5 —(O—CF 2 —CF 2 ) 2 —O—CF 2 -T
CF 3 —(O—CF 2 —CF 2 ) 2 —O—CF 2 -T
C 3 F 7 —(O—CF 2 —CF 2 ) 2 —O—CF 2 -T
C 4 F 9 —(O—CF 2 —CF 2 ) 2 —O—CF 2 -T
CF 3 —(CF 2 ) 2 —(O—CF(CF 3 )—CF 2 ) 2 —O—CF(CF 3 )-T
CF 3 —(CF 2 ) 2 —(O—CF(CF 3 )—CF 2 ) 3 —O—CF(CF 3 )-T
CF 3 —(CF 2 ) 2 —(O—CF(CF 3 )—CF 2 ) 4 —O—CF(CF 3 )-T
CF 3 —(CF 2 ) 2 —(O—CF(CF 3 )—CF 2 ) 5 —O—CF(CF 3 )-T
CF 3 —(CF 2 ) 2 —(O—CF(CF 3 )—CF 2 ) 6 —O—CF(CF 3 )-T
and mixtures thereof,
T having the meaning as defined in claim 1 .
4. The dental composition of claim 1 further comprising at least one of the following components:
a Si-containing surfactant as component (D1),
a hydrocarbon surfactant as component (D2),
a filler as component (E),
additives as component (F) selected from retarder(s), rheology modifier(s), inhibitor(s), pigment(s), plastizer(s), dye(s), pigment(s), odorous substance(s), flavouring(s), stabilizer(s), alone, in admixture or combination.
5. The dental composition of claim 4 , wherein the components are present in the following amounts:
Component (A): from about 5 wt.-% to about 97 wt.-%,
Component (B): from about 0.1 wt.-% to about 35 wt.-%,
Component (C): from about 0.001 wt.-% to about 7.5 wt.-%,
Component (D1): from 0 wt.-% to about 7 wt.-%,
Component (D2): from 0 wt.-% to about 20 wt.-%,
Component (E): from 0 wt.-% to about 80 wt.-%,
Component (F): from 0 wt.-% to about 50 wt.-%,
wt.-% with respect to the weight of the whole composition.
6. The dental composition of claim 5 , wherein component (D1) is selected from
where each R is independently a monovalent hydrocarbyl radical with 1 to 22 C-atoms, R 1 is a divalent hydrocarbylene radical 1 to 26 C-atoms, each R 2 is independently hydrogen or a lower hydroxyalkyl radical, R 3 is hydrogen or a monovalent hydrocarbyl radical with 1 to 22 C-atoms, n and b are independently greater than or equal to 0, and m and a are independently greater than or equal to 1,
or
Q-P—(OC n H 2n ) x —OZ, in which Q stands for R 3 Si— or R 3 Si—(R′—SiR 2 ) a —R′—SiR″ 2 —
where R in the molecule can be the same or different and can be an aliphatic C1-C18, a cycloaliphatic C6-C12 or an aromatic C6-C12 hydrocarbon radical, which can optionally be substituted by halogen atoms, R′ is a C1-C14 alkylene group, R″ is R in the case of a≠0 or is R or R 3 SiR′ in the case of a=0, and a=0-2; P represents a C2-C18 alkylene group or A-R′″, where A represents a C2-C18 alkylene group and R′″ a functional group selected from: —NHC(O)—, —NHC(O)—(CH 2 ) n-1 —, —NHC(O)C(O)—, —NHC(O)(CH 2 ) v C(O)—, —OC(O)—, —OC(O)—(CH 2 ) n-1 —, —OC(O)C(O)—, —OC(O)(CH 2 ) v C(O)—, —OCH 2 CH(OH)CH 2 OC(O)(CH 2 ) n-1 —, —OCH 2 CH(OH)CH 2 OC(O)(CH 2 ) v C(O)— with v=1-12; Z is H or a C1-C4 alkyl radical or a C1-C4 acyl radical; x is a number from 1 to 200 and n a number from 1 to 6.
7. The dental composition of claim 5 , wherein component (D1) is selected from
Q-P—(OC n H 2n ) x —OT,
Q being R 3 —Si— or R 3 —Si—(R′—SiR 2 ) a —R′—SiR″ 2 ,
where each R in the molecule can be the same or different and stands for an aliphatic C 1 -C 18 , a cycloaliphatic C 6 -C 12 or an aromatic C 6 -C 12 hydrocarbon radical, which can optionally be substituted by halogen atoms; R′ is a C 1 -C 14 alkylene group; R″ is R in the case of a≠0 or is R or R 3 SiR′ in the case of a=0, and a ═0 to 2; P stands for a C 2 -C 18 alkylene group, or A-R′″, where A represents a C 2 -C 18 alkylene group and R′″ a functional group from the following list: —NHC(O)—, —NHC(O)— (CH 2 ) n-1 —, —NHC(O)C(O)—, —NHC(O)(CH 2 ) v C(O)—, —OC(O)—, —OC(O)—(CH 2 ) n-1 —, —OC(O)C(O)—, —OC(O)(CH 2 ) v C(O)—, —OCH 2 CH(OH)CH 2 OC(O)(CH 2 ) n-1 —, —OCH 2 CH(OH)CH 2 OC(O)(CH 2 ) v C(O)— with v=1 to about 12; T is H or stands for a C1 to C4 alkyl radical or a C1 to C4 acyl radical; x stands for a number from 1 to about 200 and n stands for an average number from 1 to about 6.
8. The curable dental composition of claim 1 , wherein component (A) is curable via a ring-opening polymerization reaction or via a hydrosilation reaction or via condensation reaction or via ring-opening metathesis reaction.
9. A kit of parts comprising a base paste and a catalyst paste separated from each other before use, wherein the base paste comprises component (A) and the catalyst paste comprises component (B) and wherein component (C), (D1), (D2), (E), and (F), if present, can be present either in the base paste or the catalyst paste or the base paste and the catalyst paste, wherein components (A) to (F) are as described in claim 4 .
10. A curable dental composition comprising
a curable polyether group containing polymer as component (A), component (A) being a compound comprising polyalkylene oxide moieties,
an initiator capable of initiating a curing reaction of component (A) as component (B),
an F-containing compound as component (C),
wherein the F-containing compound is selected from the group of
Rf—O—CF 2 -T, with Rf being a linear or branched per- or partly fluorinated alkyl chain (C1 to C6), which can be interrupted by oxygen atoms,
Rf—O—CF 2 —CF 2 -T, with Rf being a linear or branched per- or partly fluorinated alkyl chain (C1 to C6), which can be interrupted by oxygen atoms,
Rf—O—CF 2 —CHF-T, with Rf being a linear or branched per- or partly fluorinated alkyl chain (C1 to C6), which can be interrupted by oxygen atoms,
Rf—O—CF 2 —CHF—CF 2 -T, with Rf being a linear or branched per- or partly fluorinated alkyl chain (C1 to C6), which can be interrupted by oxygen atoms,
Rf—(O—CF 2 —CF 2 —CF 2 ) n —O—CF 2 —CF 2 -T, with n=1 to 25 and Rf being a linear or branched per- or partly fluorinated alkyl chain (C1 to C6), wherein the per- or partly fluorinated alkyl chain can be interrupted by O atoms,
T-CF 2 —O—(CF 2 —CF 2 —O) p —(CF 2 —O)q-CF 2 -T, with p/q=0.5 to 3.0; and an molecular weight in the range of about 500 to about 4000 g/mol,
T-CF 2 —(O—CF(CF 3 )—CF 2 ) n —(O—CF 2 ) m —O—CF 2 -T, with n/m=20-40 and a molecular weight in the range of about 650 to about 3200 g/mol,
CF 3 —(CF 2 ) 2 —(OCF(CF 3 )—CF 2 ) z —O—CF(CF 3 )-T, with z=0, 1, 2, 3, 4, 5, 6, 7 or 8,
CF 3 —CHF—O—(CF 2 ) o -T, with o=1, 2, 3, 4, 5 or 6,
CF 3 —CF 2 —O—(CF 2 ) o -T, with o=1, 2, 3, 4, 5 or 6,
and mixtures thereof,
wherein T is selected from —COOR, —CONR b R c —CH 2 OH, —CF 2 OR, —CHFOH, —CHFOR, —CH 2 OR or —F.
11. The dental composition of claim 10 further comprising at least one of the following components:
an Si-containing surfactant as component (D1),
an hydrocarbon surfactant as component (D2),
filler as component (E),
additives as component (F) selected from retarder(s), rheology modifier(s), inhibitor(s), pigment(s), plastizer(s), dye(s), pigment(s), odorous substance(s), flavouring(s), stabilizer(s), alone, in admixture or combination.
12. The dental composition of claim 11 , wherein the components are present in the following amounts:
Component (A): from about 5 wt.-% to about 97 wt.-%,
Component (B): from about 0.1 wt.-% to about 35 wt.-%,
Component (C): from about 0.001 wt.-% to about 7.5 wt.-%,
Component (D1): from 0 wt.-% to about 7 wt.-%,
Component (D2): from 0 wt.-% to about 20 wt.-%,
Component (E): from 0 wt.-% to about 80 wt.-%,
Component (F): from 0 wt.-% to about 50 wt.-%,
wt.-% with respect to the weight of the whole composition.
13. The dental composition of claim 12 , wherein component (D1) is selected from
where each R is independently a monovalent hydrocarbyl radical with 1 to 22 C-atoms, R 1 is a divalent hydrocarbylene radical 1 to 26 C-atoms, each R 2 is independently hydrogen or a lower hydroxyalkyl radical, R 3 is hydrogen or a monovalent hydrocarbyl radical with 1 to 22 C-atoms, n and b are independently greater than or equal to 0, and m and a are independently greater than or equal to 1,
or
Q-P—(OC n H 2n ) x —OZ, in which Q stands for R 3 Si— or R 3 Si—(R′—SiR 2 ) a R′—SiR″ 2 —
where R in the molecule can be the same or different and can be an aliphatic C1-C18, a cycloaliphatic C6-C12 or an aromatic C6-C12 hydrocarbon radical, which can optionally be substituted by halogen atoms, R′ is a C1-C14 alkylene group, R″ is R in the case of a≠0 or is R or R 3 SiR′ in the case of a=0, and a=0-2; P represents a C2-C18 alkylene group or A-R′″, where A represents a C2-C18 alkylene group and R′″ a functional group selected from: —NHC(O)—, —NHC(O)—(CH 2 ) n-1 —, —NHC(O)C(O)—, —NHC(O)(CH 2 ) v C(O)—, —OC(O)—, —OC(O)—(CH 2 ) n-1 —, —OC(O)C(O)—, —OC(O)(CH 2 ) v C(O)—, —OCH 2 CH(OH)CH 2 OC(O)(CH 2 ) n-1 —, —OCH 2 CH(OH)CH 2 OC(O)(CH 2 ) v C(O)— with v=1-12; Z is H or a C1-C4 alkyl radical or a C1-C4 acyl radical; x is a number from 1 to 200 and n a number from 1 to 6.
14. The dental composition of claim 12 , wherein component (D1) is selected from
Q-P—(OC n H 2n ) x —OT,
Q being R 3 —Si— or R 3 —Si—(R′—SiR 2 ) a —R′—SiR″ 2 ,
where each R in the molecule can be the same or different and stands for an aliphatic C 1 -C 18 , a cycloaliphatic C 6 -C 12 or an aromatic C 6 -C 12 hydrocarbon radical, which can optionally be substituted by halogen atoms; R′ is a C 1 -C 14 alkylene group; R″ is R in the case of a≠0 or is R or R 3 SiR′ in the case of a=0, and a ═0 to 2; P stands for a C 2 -C 18 alkylene group, or A-R′″, where A represents a C 2 -C 18 alkylene group and R′″ a functional group from the following list: —NHC(O)—, —NHC(O)— (CH 2 ) n-1 —, —NHC(O)C(O)—, —NHC(O)(CH 2 ) v C(O)—, —OC(O)—, —OC(O)—(CH 2 ) n-1 —, —OC(O)C(O)—, —OC(O)(CH 2 ) v C(O)—, —OCH 2 CH(OH)CH 2 OC(O)(CH 2 ) n-1 —, —OCH 2 CH(OH)CH 2 OC(O)(CH 2 ) v C(O)— with v=1 to about 12; T is H or stands for a C1 to C4 alkyl radical or a C1 to C4 acyl radical; x stands for a number from 1 to about 200 and n stands for an average number from 1 to about 6.
15. The curable dental composition of claim 10 , wherein component (A) is curable via a ring-opening polymerization reaction or via a hydrosilation reaction or via condensation reaction or via ring-opening metathesis reaction.
16. A kit of parts comprising a base paste and a catalyst paste separated from each other before use, wherein the base paste comprises component (A) and the catalyst paste comprises component (B) and wherein component (C), (D1), (D2), (E), and (F), if present, can be present either in the base paste or the catalyst paste or the base paste and the catalyst paste, wherein components (A) to (F) are as described in claim 11 .
17. A curable dental composition comprising
a curable polyether group containing polymer as component (A), component (A) being a compound comprising polyalkylene oxide moieties,
an initiator capable of initiating a curing reaction of component (A) as component (B),
an F-containing compound as component (C),
wherein the F-containing compound is selected from the group of
CF 3 —O—CF 2 —O—CF 2 —CF 2 —O—CHF-T
CF 3 —(O—CF 2 ) 2 —O—CF 2 —CF 2 —O—CHF-T
CF 3 —(O—CF 2 ) 3 —O—CF 2 —CF 2 —O—CHF-T
CF 3 —O—CF 2 —O—CF 2 —CF 2 —O—CHF—CF 2 -T
CF 3 —(O—CF 2 ) 2 —O—CF 2 —CF 2 —O—CHF—CF 2 -T
CF 3 —(O—CF 2 ) 3 —O—CF 2 —CF 2 —O—CHF—CF 2 -T
C 3 F 7 —O—CF 2 —CHF-T
CF 3 —O—CF 2 —O—CF 2 —CF 2 —O—CF 2 —CHF-T
CF 3 —(O—CF 2 ) 2 —O—CF 2 —CF 2 —O—CF 2 —CHF-T
CF 3 —(O—CF 2 ) 3 —O—CF 2 —CF 2 —O—CF 2 —CHF-T
C 3 F 7 —O—CF 2 —CHF—CF 2 -T
CF 3 —O—CF 2 —CF 2 —CF 2 —O—CF 2 —CHF—CF 2 -T
CF 3 —O—CF 2 —O—CF 2 —CF 2 —O—CF 2 —CHF—CF 2 -T
CF 3 —(O—CF 2 ) 2 —O—CF 2 —CF 2 —O—CF 2 —CHF—CF 2 -T
CF 3 —(O—CF 2 ) 3 —O—CF 2 —CF 2 —O—CF 2 —CHF—CF 2 -T
CF 3 —CFH—O—(CF 2 ) 3 -T
CF 3 —CFH—O—(CF 2 ) 5 -T
CF 3 —CF 2 —O—(CF 2 ) 3 -T
CF 3 —CF 2 —O—(CF 2 ) 5 -T
Rf—(O—CF 2 —CF 2 —CF 2 ) n —O—CF 2 —CF 2 -T, with n=1 to 25 and Rf being a linear or branched per- or partly fluorinated alkyl chain (C1 to C6), wherein the per- or partly fluorinated alkyl chain can be interrupted by O atoms,
T-CF 2 —O—(CF 2 —CF 2 —O) p —(CF 2 —O) q —CF 2 -T, with p/q=0.5 to 3.0 and an molecular weight in the range of about 500 to about 4000 g/mol,
T-CF 2 —(O—CF(CF 3 )—CF 2 ) n —(O—CF 2 ) m —O—CF 2 -T, with n/m=about 20 to 40 and a molecular weight in the range of about 650 to about 3200 g/mol,
and mixtures thereof,
wherein T is selected from —COOR, —CONR b R c —CH 2 OH, —CF 2 OR, —CHFOH, —CHFOR, —CH 2 OR or —F.
18. The dental composition of claim 17 further comprising at least one of the following components:
a Si-containing surfactant as component (D1),
a hydrocarbon surfactant as component (D2),
a filler as component (E),
additives as component (F) selected from retarder(s), rheology modifier(s), inhibitor(s), pigment(s), plastizer(s), dye(s), pigment(s), odorous substance(s), flavouring(s), stabilizer(s), alone, in admixture or combination.
19. The dental composition of claim 18 , wherein the components are present in the following amounts:
Component (A): from about 5 wt.-% to about 97 wt.-%,
Component (B): from about 0.1 wt.-% to about 35 wt.-%,
Component (C): from about 0.001 wt.-% to about 7.5 wt.-%,
Component (D1): from 0 wt.-% to about 7 wt.-%,
Component (D2): from 0 wt.-% to about 20 wt.-%,
Component (E): from 0 wt.-% to about 80 wt.-%,
Component (F): from 0 wt.-% to about 50 wt.-%,
wt.-% with respect to the weight of the whole composition.
20. The dental composition of claim 19 , wherein component (D1) is selected from
where each R is independently a monovalent hydrocarbyl radical with 1 to 22 C-atoms, R 1 is a divalent hydrocarbylene radical 1 to 26 C-atoms, each R 2 is independently hydrogen or a lower hydroxyalkyl radical, R 3 is hydrogen or a monovalent hydrocarbyl radical with 1 to 22 C-atoms, n and b are independently greater than or equal to 0, and m and a are independently greater than or equal to 1,
or
Q-P—(OC n H 2n ) x —OZ, in which Q stands for R 3 Si— or R 3 Si—(R′—SiR 2 ) a —R′—SiR″ 2 —
where R in the molecule can be the same or different and can be an aliphatic C1-C18, a cycloaliphatic C6-C12 or an aromatic C 6 -C 12 hydrocarbon radical, which can optionally be substituted by halogen atoms, R′ is a C1-C14 alkylene group, R″ is R in the case of a≠0 or is R or R 3 SiR′ in the case of a=0, and a=0-2; P represents a C2-C18 alkylene group or A-R′″, where A represents a C2-C18 alkylene group and R′″ a functional group selected from: —NHC(O)—, —NHC(O)—(CH 2 ) n-1 —, —NHC(O)C(O)—, —NHC(O)(CH 2 ) v C(O)—, —OC(O)—, —OC(O)—(CH 2 ) n-1 —, —OC(O)C(O)—, —OC(O)(CH 2 ) v C(O)—, —OCH 2 CH(OH)CH 2 OC(O)(CH 2 ) n-1 —, —OCH 2 CH(OH)CH 2 OC(O)(CH 2 ) v C(O)— with v=1-12; Z is H or a C1-C4 alkyl radical or a C1-C4 acyl radical; x is a number from 1 to 200 and n a number from 1 to 6.
21. The dental composition of claim 19 , wherein component (D1) is selected from
Q-P—(OC n H 2n ) x —OT,
Q being R 3 —Si— or R 3 —Si—(R′—SiR 2 ) a —R′—SiR″ 2 ,
where each R in the molecule can be the same or different and stands for an aliphatic C 1 -C 18 , a cycloaliphatic C 6 -C 12 or an aromatic C 6 -C 12 hydrocarbon radical, which can optionally be substituted by halogen atoms; R′ is a C 1 -C 14 alkylene group; R″ is R in the case of a≠0 or is R or R 3 SiR′ in the case of a=0, and a ═0 to 2; P stands for a C 2 -C 18 alkylene group, or A-R′″, where A represents a C 2 -C 18 alkylene group and R′″ a functional group from the following list: —NHC(O)—, —NHC(O)— (CH 2 ) n-1 —, —NHC(O)C(O)—, —NHC(O)(CH 2 ) v C(O)—, —OC(O)—, —OC(O)—(CH 2 ) n-1 —, —OC(O)C(O)—, —OC(O)(CH 2 ) v C(O)—, —OCH 2 CH(OH)CH 2 OC(O)(CH 2 ) n-1 —, —OCH 2 CH(OH)CH 2 OC(O)(CH 2 ) v C(O)— with v=1 to about 12; T is H or stands for a C1 to C4 alkyl radical or a C1 to C4 acyl radical; x stands for a number from 1 to about 200 and n stands for an average number from 1 to about 6.
22. The curable dental composition of claim 17 , wherein component (A) is curable via a ring-opening polymerization reaction or via a hydrosilation reaction or via condensation reaction or via ring-opening metathesis reaction.
23. A kit of parts comprising a base paste and a catalyst paste separated from each other before use, wherein the base paste comprises component (A) and the catalyst paste comprises component (B) and wherein component (C), (D1), (D2), (E), and (F), if present, can be present either in the base paste or the catalyst paste or the base paste and the catalyst paste, wherein components (A) to (F) are as described in claim 18 .